Sodium periodate → HCID 59909833, compound

HRID 1279896Notes

Reaction equation

HRID 1279896 reaction equation
[CH3:1][N:2]([CH3:22])[C:3]([C:5]1[N:6]=[C:7]([C@H:10]([CH2:19][CH:20]=C)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:8][CH:9]=1)=[O:4].I([O-])(=O)(=O)=[O:24].[Na+]>CC(C)=O.O.[Os](=O)(=O)(=O)=O.C(O)(C)(C)C>[CH3:1][N:2]([CH3:22])[C:3]([C:5]1[N:6]=[C:7]([C@H:10]([CH2:19][CH:20]=[O:24])[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[O:8][CH:9]=1)=[O:4]

Participants

7

Reactant 2

HCID 23667635Sodium periodateHCID 59909781HCID 59909781, compound

Product 1

HCID 59909833HCID 59909833, compoundYield 86.1%

Reagents, catalysts & solvents 4

HCID 6386tert-ButanolCatalystHCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl (3R)-3-{4-[(dimethylamino)carbonyl]-1,3-oxazol-2-yl}-5-hexenoate (Preparation 117) (1.0 g, 3.24 mmol) in acetone (20 ml) and water (20 ml) was treated with osmium tetroxide, 2.5 % wt in tert-butanol (500 μl, 0.04 mmol) and stirred at room temperature for 5 minutes. Sodium periodate (2.13 g, 10.00 mmol) was added and the reaction mixture stirred for 2 hours. The reaction mixture was partitioned between ethyl acetate and aqueous sodium thiosulphate solution (20 % wt). The organic layer was washed with water (×2) and brine, dried over anhydrous sodium sulphate and filtered. The solvent was removed under reduced pressure to afford the title compound as a colourless oil (866 mg).

Workup

  1. stirringthe reaction mixture stirred for 2 hours
  2. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium thiosulphate solution (20 % wt)
  3. washThe organic layer was washed with water (×2) and brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-81feba3fbf3344cdb2f2a93f6ac68b16
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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